CAS 1225-56-5 (3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamine (HCID 6433351)

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Basic information

CAS: 1225-56-5
Standard SMILES: CNCC/C=C1\c2ccccc2COc2ccccc21
InChIKey: HVKCEFHNSNZIHO-MHWRWJLKSA-N
Molecular formula: C18H19NO
Average molar mass: 265.3 g/mol
Monoisotopic mass: 265.14666423

Overview

(E)-desmethyldoxepin is the (E)-isomer of desmethyldoxepin.

Names & identifiers

Preferred name: (3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamine
IUPAC: (3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N-methylpropan-1-amine
English name: Desmethyldoxepin
Molecular formula: C18H19NO
Molecular weight: 265.35

Names & synonyms

trans-DesmethyldoxepinDesmethyldoxepin, (E)-Doxepin impurity C67035-76-1J7JTC0A5D6DTXSID60217319(E)-3-(Dibenzo(b,E)oxepin-11(6H)-ylidene)-N-methylpropan-1-amine1-Propanamine, 3-dibenz(b,E)oxepin-11(6H)-ylidene-N-methyl-, (3E)-1-Propanamine, 3-dibenz(b,E)oxepin-11(6H)-ylidene-N-methyl-, (E)-(E)-3-(Dibenzo[b,e]oxepin-11(6H)-ylidene)-N-methylpropan-1-amineRefChem:906009DTXCID10139810

Show more names

NORDOXEPINDemethyldoxepinDesmethyldoxepin solutionNordoxepin 13CD3DesmethyldoxepinDesmethyldoxepineMonodesmethyldoxepinDesmethyldoxepin (cis/trans)(E,Z)-3-(Dibenzo[b,e]oxepin-11(6H)-Doxepin EP Impurity C(Desmethyldoxepine)

(3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamine(E)-Desmethyldoxepin(3E)-3-(dibenzo[b,e]oxepin-11(6H)-ylidene)-N-methylpropan-1-amineUNII-F498JSH8RRUNII-J7JTC0A5D6(E)desmethyldoxepinDoxepin hydrochloride impurity C [EP]DOXEPIN_met004

Properties

Computed structural properties

XLogP: 3.8
Topological polar surface area: 21.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 20
Formal charge: 0
Complexity: 338

Experimental & physicochemical properties

Collision Cross Section157.72 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 63 · 63-65℃
Boiling point: 408.57 °C · 408.57°C (rough estimate)
Density: 1.0629 · 1.0629 (rough estimate)
refractive index: 1.51 · 1.5100 (estimate)
Flash point: 9 ℃ · 9℃
storage temp.: -20 °C · -20°C
solubility: DMSO (Slightly), Methanol (Slightly)
pka: 9.75 · pKa 9.75(I=0.00 t=25.0) (Uncertain)
form: Solid
color: White
Water Solubility: 104.8 mg/L · 104.8mg/L(25 ºC)
Major Application: clinical testing

Safety & regulation

Safety data

wgk: 2
ridadr: UN1230 - class 3 - PG 2 - Methanol, solution
risk_code: 11-23/24/25-39/23/24/25
Signal word: Danger
Symbol(GHS): GHS02,GHS06,GHS08
hazard_code: F,T
safety_code: 7-16-36/37-45
Storage Class: 3 - Flammable liquids
target organs: Eyes
Hazard statements: H225-H301+H311+H331-H370
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Precautionary statements: P210-P260-P280-P301+P310-P311

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system.

Applications · 2 items

UsesDesmethyldoxepin solution may be used as an internal standard in the high performance liquid chromatographic (HPLC) determination of bupivacaine in samples of human serum.

General DescriptionDesmethyldoxpein is the primary urinary metabolite of doxepin, a tricyclic antidepressant used for the treatment of sleep maintenance and sold under trade names such as Silenor and Aponal. This analytical reference standard is suited for use in LC/MS or GC/MS methods for urine drug testing, clinical toxicology, and forensic analysis applications.